CN101805261A - Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae - Google Patents

Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae Download PDF

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Publication number
CN101805261A
CN101805261A CN201010135116A CN201010135116A CN101805261A CN 101805261 A CN101805261 A CN 101805261A CN 201010135116 A CN201010135116 A CN 201010135116A CN 201010135116 A CN201010135116 A CN 201010135116A CN 101805261 A CN101805261 A CN 101805261A
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China
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deionized water
chlorogenic acid
extraction
solvent
temperature
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CN201010135116A
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王平
李建
李雪松
卢义德
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HANZHONG TRG BIOTECH CO Ltd
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HANZHONG TRG BIOTECH CO Ltd
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Abstract

The invention relates to a method for preparing competitive products of chlorogenic acid by folium cortex eucommiae, comprising the technological flows of normal temperature soaking and extraction by adopting deionized water, squeezing (or centrifugalizing), macroporous absorption column chromatography and enrichment, acetic ether extraction and deionized water recrystallization, and taking a series of protective measures aiming at the instability of easy decomposition of target product chlorogenic acid, such as controlling temperature and pH value, adding antioxidant, shortening production cycle and the like. The method has the characteristics of low cost, easy operation, high recovery rate and high content, and opens up a new approach for factorial large-scale development and full utilization of eucommia ulmoides resource.

Description

A kind of method of preparing chlorogenic acid from eucommia leaves elaboration
Technical field
The present invention relates to a kind of method of preparing chlorogenic acid from eucommia leaves elaboration.
Background technology:
The depside that chlorogenic acid (Chlorogenic acid) is made up of coffic acid (Cafieic acid) and quininic acid (Quinic acid), the different name chlorogenic acid, chemical name 3-O-caffeoylquinic acids (3-O-Cafeoylquinic acid), molecular formula is C 16H 18O 9, relative molecular mass 354.30 is a kind of phenylpropyl alcohol chlorins compounds that plant materials produces through shikimic acid pathway in the aerobic repiration process.Chlorogenic acid is a kind of important biological material, have antibiotic, antiviral, increase effects such as white cell, hepatic cholagogic, antitumor, hypotensive, reducing blood-fat, removing free radical and stimulating central nervous system system.It is one of effective constituent of many Chinese medicinal materialss, is again the quality index of some patent medicine.Chlorogenic acid is widely used in industries such as medicine, daily-use chemical industry and food.Though chlorogenic acid is present in all kinds of plants comparatively at large, the higher plant of content is actually rare.Chlorogenic acid contents is higher in studies show that in recent years, the bark of eucommia (Eucommia ulmoides), and the content in its middle period is about 1-3%.As the medicinal history that the centuries has been arranged, cultivated area is quite extensive in China for the bark of eucommia, and the whole nation has 200,000 squares of hectares of bark of eucommia woods approximately, can produce the millions of tons of leaf every year.But the Development and Production of bark of eucommia high-end product lags behind at present, the particularly Separation ﹠ Purification of single component; Low-end product has only fragmentary production, cause the waste of a large amount of eucommia resources, make the condition that faces a difficult selection, the bark of eucommia production base that grows up over, this mainly is because some research only rests on laboratory stage, lack the complete set technology that is applied to actual production, extract medicinal even chemical pure chlorogenic acid if can be used in, will produce huge social and economic benefit undoubtedly.Main extracting method in the Folium Eucommiae chlorogenic acid research at present has: solvent-extraction process, ultrasonic extraction, supercritical CO 2Method, extraction method enzyme extraction method etc.; The method for purifying and separating of chlorogenic acid has: polyamide column chromatography method, ultra-filtration membrane partition method, lead salt precipitation separation, solvent extraction and separation method, macroporous resin partition method.But problems such as aforesaid method exists, and investment is big, technical requirements is high, heavy-metal residual and purity are low, the large-scale production difficulty.
The objective of the invention is to utilize in these years the research basis of chlorogenic acid extraction separation in the Folium Eucommiae, a kind of chlorogenic acid elaboration preparation method with low cost, easy to operate, high-content characteristics is provided.For a new approach is opened up in the development and use of Folium Eucommiae.
---the deionized water soak at room temperature extracts---squeezes (or centrifugal)---column chromatography enrichment---solvent extraction---coarse crystallization---recrystallization (elaboration) in the technical process of preparing chlorogenic acid from eucommia leaves elaboration of the present invention: Folium Eucommiae coarse reduction;
Concrete grammar is as follows:
(1) Folium Eucommiae coarse reduction;
(2) the deionized water soak at room temperature extracts, and temperature 30-40 ℃, regulate pH value to 3.0-3.5, time 30-60 minute/time, repeat 3-4 time,
(3) vat liquor clarification back, adds the reductive agent vacuum and low temperature and concentrates again through the 30-50% ethanol elution with the absorption of macroporous resin upper prop, and wherein macroporous resin is a kind of of AAS, NKA-II, NKA-9, and reductive agent is a kind of of sodium bisulfite, Sulfothiorine,
(4) ethyl acetate extraction elutriant cryoconcentration is to proportion 1.05-1.10, extract with equimultiple water saturation solvent normal temperature, combining extraction liquid, cryoconcentration is to muddy the appearance arranged after reclaiming solvent, leave standstill crystallization, wherein selected extraction solvent is a kind of in propyl carbinol, acetone, the vinyl acetic monomer, also can be its several mixing
(5) recrystallization deionized water 1: 2-1: 4 thermosols, filter stand at low temperature crystallization, cryodrying, finished product.
The present invention adopts the deionized water soak at room temperature to extract; squeezing (or centrifugal); the technical process of the enrichment of macroporous absorption column chromatography, solvent extraction, deionized water recrystallization; taked serial sfgd. at the labile unstable of target product chlorogenic acid: controlled temperature, pH value, adding antioxidant, shortening production cycle etc.; have low-cost, easy to operate, high-recovery and high-load characteristics, for the batch production scale development, make full use of eucommia resource and open up a new approach.
Embodiment
Below in conjunction with three embodiment, the invention will be further described.Embodiment 1. Folium Eucommiae 1000Kg, coarse reduction adds in the 8000L deionized water, and 30 ℃ of soaking temperatures drained after 30 minutes, added deionized water 6000L continuation temperature and soaked, and repeated 4 times.Folium Eucommiae after squeezing is soaked, merge soaked extracting solution, add hydrochloric acid by 1: 5 and adjust pH value to 3.0, go up after filtering adsorption column NKA-9, multicolumn is applied mechanically, saturated to adsorbing, doubly measure wash-out with 30% ethanol, elutriant adds 0.5% (W/V) sodium bisulfite, decompression recycling ethanol, low temperature (T≤60 ℃) is concentrated into proportion 1.05, with 3-4 normal temperature extraction of equimultiple water saturation vinyl acetic monomer, merges vinyl acetic monomer and reclaims low temperature behind the solvent (T≤50 ℃) mutually and be concentrated into muddy appearance, left standstill crystallization 12 hours, recrystallization gets white crystals product 6.4Kg, HPLC content: 98.8%.
Embodiment 2. Folium Eucommiae 1500Kg, coarse reduction, add soaking at room temperature in the 12000L deionized water, intermittently stir 30 ℃ of temperature, drain after 40 minutes, add deionized water 9000L continuation temperature and soak, repeat 4 times, the Folium Eucommiae after squeezing is soaked, merge soaked extracting solution, adjust pH value to 3.0 with 1: 5 hydrochloric acid.Go up after filtering adsorption column AAS, multicolumn is applied mechanically, and is saturated to adsorbing, 30% ethanol is doubly measured wash-out, elutriant adds 0.5% (W/V) sodium bisulfite, 0.3% Sulfothiorine, decompression recycling ethanol, and low temperature (T≤60 ℃) is concentrated into proportion 1.06, with 3-4 normal temperature extraction of equimultiple water saturation vinyl acetic monomer, merge vinyl acetic monomer and reclaim low temperature behind the solvent (T≤50 ℃) mutually and be concentrated into muddy the appearance, left standstill crystallization 12 hours, recrystallization, get white crystals product 9Kg, HPLC content: 98.2%.
Embodiment 3. Folium Eucommiae 1000Kg, coarse reduction, add the 8000L deionized water, 40 ℃ of soaking temperatures drained after 30 minutes, adding deionized water 6000L continuation temperature soaks, repeat 4 times, the Folium Eucommiae after squeezing is soaked merges soaked extracting solution, hydrochloric acid was adjusted pH value to 3.0 in 1: 5, go up after filtering adsorption column NKA-II, multicolumn is applied mechanically, and is saturated to adsorbing, 30% ethanol is doubly measured wash-out, elutriant adds 0.4% (W/V) sodium bisulfite, decompression recycling ethanol, and low temperature (T≤60 ℃) is concentrated into proportion 1.10, with 3-4 normal temperature extraction of equimultiple water saturation vinyl acetic monomer, merge vinyl acetic monomer and reclaim low temperature behind the solvent (T≤50 ℃) mutually and be concentrated into muddy the appearance, left standstill crystallization 12 hours, the deionized water recrystallization, get white crystals product 6.4Kg, HPLC content: 98.5%.
Can extract gutta-percha after the slag squeezing.

Claims (1)

1. the method for a preparing chlorogenic acid from eucommia leaves elaboration, it is with the Folium Eucommiae coarse reduction---the deionized water soak at room temperature extracts---squeezing (or centrifugal)---column chromatography enrichment---solvent extraction---coarse crystallization---recrystallization (elaboration);
It is characterized in that:
(1) Folium Eucommiae coarse reduction;
(2) the deionized water soak at room temperature extracts, and temperature 30-40 ℃, regulate pH value to 3.0-3.5, time 30-60 minute/time, repeat 3-4 time,
(3) vat liquor clarification back, adds the reductive agent vacuum and low temperature and concentrates again through the 30-50% ethanol elution with the absorption of macroporous resin upper prop, and wherein macroporous resin is a kind of of AAS, NKA-II, NKA-9, and reductive agent is a kind of of sodium bisulfite, Sulfothiorine,
(4) ethyl acetate extraction elutriant cryoconcentration is to proportion 1.05-1.10, extract with equimultiple water saturation solvent normal temperature, combining extraction liquid, cryoconcentration is to muddy the appearance arranged after reclaiming solvent, leave standstill crystallization, wherein selected extraction solvent is a kind of in propyl carbinol, acetone, the vinyl acetic monomer, also can be its several mixing
(5) recrystallization deionized water 1: 2-1: 4 thermosols, filter stand at low temperature crystallization, cryodrying, finished product.
CN201010135116A 2010-03-26 2010-03-26 Method for preparing competitive product of chlorogenic acid by folium cortex eucommiae Pending CN101805261A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102351700A (en) * 2011-08-15 2012-02-15 中国科学院过程工程研究所 Method for separating and purifying chlorogenic acid from eucommia ulmoides leaves
CN103012518A (en) * 2012-12-14 2013-04-03 湘西自治州奥瑞克医药化工有限责任公司 Production process for simultaneously extracting asperuloside and chlorogenic acid from folium cortex eucommiae
CN103992224A (en) * 2014-05-05 2014-08-20 四川九章生物化工科技发展有限公司 Method for extracting chlorogenic acid from eucommia ulmoides leaves
CN105085265A (en) * 2014-05-09 2015-11-25 四川九章生物化工科技发展有限公司 Chlorogenic acid raw material or bulk pharmaceutical chemicals and preparation method and quality detection method therefor
US20170050915A1 (en) * 2014-05-09 2017-02-23 Sichuan Jiuzhang Bilogical Science Adn Technology Co., Ltd. Crystalline form of chlorogenic acid and preparation method thereof
CN109111364A (en) * 2017-06-22 2019-01-01 中国烟草总公司广东省公司 A kind of method of high-pressure pulse electric combination microwave, ultrasonic wave extraction tobacco waste Content of Chlorogenic Acid
US10189769B2 (en) 2014-11-26 2019-01-29 Sichuan Jiuzhang Biological Science And Technology Co., Ltd. Method for preparation of pharmaceutically acceptable chlorogenic acid
CN110240544A (en) * 2019-06-03 2019-09-17 西北农林科技大学 A kind of chlorogenic acid method for extraction and purification and application
CN110483294A (en) * 2019-09-06 2019-11-22 湖南理工学院 One-step method multistage centrifugal fractional extraction separating chlorogenic acid from eucommia ulmoides extracts

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1616402A (en) * 2003-12-12 2005-05-18 贵州家诚药业有限责任公司 Method for extracting and separating chlorogenic acid
CN1687435A (en) * 2005-04-14 2005-10-26 四川九章生物化工科技发展有限公司 Technique for producing high purity chlorogenic acid in industrialization scale
CN101602668A (en) * 2009-07-13 2009-12-16 江西省科学院应用化学研究所 The method that a kind of chlorogenic acid extracts

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1616402A (en) * 2003-12-12 2005-05-18 贵州家诚药业有限责任公司 Method for extracting and separating chlorogenic acid
CN1687435A (en) * 2005-04-14 2005-10-26 四川九章生物化工科技发展有限公司 Technique for producing high purity chlorogenic acid in industrialization scale
CN101602668A (en) * 2009-07-13 2009-12-16 江西省科学院应用化学研究所 The method that a kind of chlorogenic acid extracts

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102351700B (en) * 2011-08-15 2013-06-05 中国科学院过程工程研究所 Method for separating and purifying chlorogenic acid from eucommia ulmoides leaves
CN102351700A (en) * 2011-08-15 2012-02-15 中国科学院过程工程研究所 Method for separating and purifying chlorogenic acid from eucommia ulmoides leaves
CN103012518A (en) * 2012-12-14 2013-04-03 湘西自治州奥瑞克医药化工有限责任公司 Production process for simultaneously extracting asperuloside and chlorogenic acid from folium cortex eucommiae
JP2017520616A (en) * 2014-05-05 2017-07-27 スーチョアン チウチャン バイオロジカル サイエンス アンド テクノロジー カンパニー リミテッド Extraction method of chlorogenic acid from Tochu leaves
CN103992224A (en) * 2014-05-05 2014-08-20 四川九章生物化工科技发展有限公司 Method for extracting chlorogenic acid from eucommia ulmoides leaves
CN103992224B (en) * 2014-05-05 2016-08-17 四川九章生物化工科技发展有限公司 A kind of method from extracting chlorogenic acid from Eucommia leaves
CN105085265A (en) * 2014-05-09 2015-11-25 四川九章生物化工科技发展有限公司 Chlorogenic acid raw material or bulk pharmaceutical chemicals and preparation method and quality detection method therefor
JP2017517476A (en) * 2014-05-09 2017-06-29 スーチョアン チウチャン バイオロジカル サイエンス アンド テクノロジー カンパニー リミテッド Chlorogenic acid crystal form and preparation method thereof
US20170050915A1 (en) * 2014-05-09 2017-02-23 Sichuan Jiuzhang Bilogical Science Adn Technology Co., Ltd. Crystalline form of chlorogenic acid and preparation method thereof
CN105085265B (en) * 2014-05-09 2017-11-07 四川九章生物科技有限公司 A kind of chlorogenic acid raw material or bulk drug and preparation method thereof and quality determining method
EP3141540A4 (en) * 2014-05-09 2018-01-03 Sichuan Jiuzhang Biological Science And Technology Co., Ltd Crystalline form of chlorogenic acid and preparation method therefor
US10246401B2 (en) * 2014-05-09 2019-04-02 Sichuan Jiuzhang Biological Science And Technology Co., Ltd. Crystalline form of chlorogenic acid and preparation method thereof
US10189769B2 (en) 2014-11-26 2019-01-29 Sichuan Jiuzhang Biological Science And Technology Co., Ltd. Method for preparation of pharmaceutically acceptable chlorogenic acid
CN109111364A (en) * 2017-06-22 2019-01-01 中国烟草总公司广东省公司 A kind of method of high-pressure pulse electric combination microwave, ultrasonic wave extraction tobacco waste Content of Chlorogenic Acid
CN109111364B (en) * 2017-06-22 2021-06-22 中国烟草总公司广东省公司 Method for extracting chlorogenic acid from tobacco waste by combining high-voltage pulsed electric field with microwaves and ultrasonic waves
CN110240544A (en) * 2019-06-03 2019-09-17 西北农林科技大学 A kind of chlorogenic acid method for extraction and purification and application
CN110483294A (en) * 2019-09-06 2019-11-22 湖南理工学院 One-step method multistage centrifugal fractional extraction separating chlorogenic acid from eucommia ulmoides extracts

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Application publication date: 20100818